Diazomethane → HCID 10421232, compound

Participants

Reaction Steps

To a solution of 490 mg (1.97 mmol) of methyl 3-hydroxy-5,6,7,8-tetrahydro-4H-isoxazolo[4,5-c]azepin-5-carboxylate (Formula II; Z=methoxycarbonyl, R3 =R4 =hydrogen) (P. Krogsgaard-Larsen, Acta Chem. Scand. B 31 (1977) 584-588) in ether (20 ml) was added an excess of diazomethane. The mixture was stirred at room temperature for 1 hour and the excess of diazomethane was destroyed by addition of glacial acetic acid. The mixture was evaporated in vacuo and the residue submitted to flash-chromatography on silica gel (eluent: toluene-ethyl acetate containing 1% of glacial acetic acid) yielding 270 mg of the title compound as a colourless oil. The oil was crystallized from toluene-light petroleum giving the analytically pure title compound. M.P. 68°-70° C. 1H NMR (CDCl3): δ4.25 (2H, s), 3.93 (3H, s), 3.66 (5H, m), 2.83 (2H, t), 1.91 (2H, m).

Provenance & Evidence